Herstellung von 1,5‐Cyclooctadiin und 1,3,5,7‐Cyclooctatetraen aus 1,5‐Cyclooctadien
1994; Wiley; Volume: 127; Issue: 8 Linguagem: Inglês
10.1002/cber.19941270829
ISSN0009-2940
AutoresHeiner Detert, Bernd Rose, W. Mayer, Herbert Meier,
Tópico(s)Chemical Synthesis and Analysis
ResumoPreparation of 1,5‐Cyclooctadiyne and 1,3,5,7‐Cyclooctatetraene from 1,5‐Cyclooctadiene Bromination of 1,5‐cyclooctadiene ( 1 ) and stepwise dehydro‐bromination first with KO t Bu and then with KO t Bu/18‐crown‐6 yields 1,5‐cyclooctadiyne ( 5 ). A prolonged interaction of the base causes a complete transformation to cyclooc‐tatetraene ( 6 ). Diyne 5 and even more the intermediate enyne 4 are highly reactive dienophiles. The cycloadducts 10 – 14 formed with 1,3‐cyclohexadiene, carbon disulfide, and tetraphenylcyclopentadienone were isolated and characterized. Treatment of 5 with titanium tetrachloride induces a vigorous polymerization.
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